Courtesy / KW Commercial Keller Williams Realty
A schooner operating out of Boothbay Harbor, Lazy Jack, was one of two that were recently acquired. Lazy Jack has been renamed Applejack.
January 12, 2023
Tour boat operators return to Maine, buying Boothbay schooners
Courtesy / Schooner Explorations of Maine LLC
Three partners jumped at the chance to buy Eastwind, the sixth schooner built by Doris and Herb Smith.
The owners of a Key West tour boat operation are returning to their Maine roots with the acquisition of passenger schooners in Boothbay Harbor.
Schooner Explorations of Maine LLC bought the schooners Lazy Jack and Eastwind, along with the business’s leases and good will, from Tom Smith for an undisclosed price.
Scott Balfour of Magnusson Balfour Commercial & Business Brokers-Keller Williams Realty brokered the business-only deal.
“The business was very well run,” Balfour told Mainebiz. “It’s a turnkey operation.”
The business was on the market for less than 30 days.
“It went fast,” Balfour said.
The listing received a lot of interest.
“We got over 14 confidentiality agreements signed,” said Balfour. “Some of those came in after the sale was pending. They’re beautiful boats and you get the beautiful harbor. It’s a dream business for many.”
Schooner Explorations of Maine LLC is owned by Paul McGrail, Sean Rowley and Rod Veal.
Early in their careers, Rowley worked at East Boothbay boatyard Paul E. Luke Inc. and McGrail worked for Southwest Harbor boatbuilder Hinckley Yachts.
Key West watersports
Since their time in Maine, Rowley and McGrail developed a long history of running tour boats in Key West, Fla.
In the late 1980s, they started Sebago Watersports, which grew from one boat — a racing catamaran built by Walter Greene of Yarmouth — to a fleet of day-charter sailing catamarans and parasail vessels.
Today, McGrail said, the business serves over 100,000 passengers per year.
Expansion to schooners
In 2004, McGrail and Rowley also partnered with a Camden business called Schooner Explorations of Maine LLC.
Schooner Explorations of Maine LLC, founded in 1988 by John McKean, operated a passenger schooner called Appledore II in Camden in the summer and Key West in the winter.
McGrail and Rowley’s partnership with McKean allowed them to take over the Appledore II’s Key West operation.
Veal, who had been serving as general manager of Sebago Watersports, became a partner in Schooner Explorations of Maine LLC.
Eastwind origins
The Appledore II was one of half a dozen schooners built by Maine residents Herb and Doris Smith, who circumnavigated the globe a number of times and wrote two books about their voyages.
The Smith family also operated their schooners as passenger vessels in Boothbay Harbor for about 50 years.
The Smiths were “icons in the Boothbay schooner industry,” said McGrail.
Courtesy / Schooner Explorations of Maine LLC
Doris Smith, left, co-owned a passenger schooner business in Boothbay Harbor for many years. Sean Rowley is one of the buyers of the Smith family’s schooners Eastwind and Lazy Jack.
The Smiths built their first schooner in the 1970s. They named five of their schooners Appledore.
In 1999, the Smiths built a sixth schooner that was similar in style to the Appledores and was named Eastwind. The Smiths also operated that one as a passenger schooner in Boothbay Harbor.
Herb and Doris Smith’s son, Tom Smith, came to own Eastwind and eventually bought another schooner operating out of Boothbay Harbor, named Lazy Jack, said McGrail.
Focus on schooners
In 2018, a large publicly traded conglomerate bought the catamaran and watersports segments of Sebago Watersports.
That gave Rowley, McGrail and Veal the chance to focus exclusively on their Schooner Explorations of Maine LLC operation as they continued to run the Appledore II in Camden and Key West.
In 2022, when Tom Smith decided to sell the Eastwind and Lazy Jack, the partners jumped on the chance to expand their schooner business.
Courtesy / KW Commercial Keller Williams Realty
Eastwind’s wheel evokes the vessel’s classic style.
“When the opportunity for East Wind and Lazy Jack was suggested to us by Tom Smith, it was a natural for us in many ways that fit with our long-term plans,” said McGrail.
The purchase was financed through Rowley’s personal resources.
The plan is to continue to operate the Appledore II in Camden. Lazy Jack will be renamed Applejack and it will continue to run from Boothbay Harbor. And they’ll continue to run another schooner they own, the Appledore Star, from Key West.
“Our goal right now is to grow the business,” said McGrail. “The only thing we want to modernize is the reservation system.”
The plan is to be in service by mid-May and run through early October in Boothbay Harbor and Camden. Some of the employees will stay on and there will likely be additional hiring.
“We are looking forward to becoming part of the Boothbay community and continuing the great tradition that the Smiths have established there,” said McGrail.
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